allyl N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-N⁵-acetyl-N⁵-benzyloxy-L-ornithinyl-glycinyl-L-3-(N-acetyl-N-benzyloxy)aminoalaninate | 1022160-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-N⁵-acetyl-N⁵-benzyloxy-L-ornithinyl-glycinyl-L-3-(N-acetyl-N-benzyloxy)aminoalaninate
• CAS: 1022160-23-1
• 化学式: C₅₈H₆₈N₆O₁₂
• 分子量: 1041.21
• InChiKey: LCYXRIXLHKGJFO-TZTPEXNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  76.0
• 可旋转键数：
  33.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  220.24
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  allyl N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-N⁵-acetyl-N⁵-benzyloxy-L-ornithinyl-glycinyl-L-3-(N-acetyl-N-benzyloxy)aminoalaninate 在 四(三苯基膦)钯 、 甲酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以94%的产率得到N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-N⁵-acetyl-N⁵-benzyloxy-L-ornithinyl-glycinyl-L-3-(N-acetyl-N-benzyloxy)aminoalanine
  参考文献：
  名称：

  Design and synthesis of a novel protected mixed ligand siderophore

  摘要：

  A novel siderophore analog (4) has been designed to facilitate iron transport-mediated drug delivery and drug release. This mixed ligand siderophore analog includes three bidentate ligands intended to octahedrally coordinate iron (III). The ligands include a 2,3-dihydroxy benzoic acid moiety, N(5)-acetyl-N(5)-hydroxy-L-ornithine, and a beta-N-hydroxy-alpha,beta-diaminopropionic acid derivative. The total synthesis of 15, a form of 4 that is suitably protected, yet contains a free carboxylic acid for subsequent drug conjugation, is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.007
• 作为产物：
  描述：

  allyl L-3-(N-acetyl-N-benzyloxy)aminoalaninate 、 N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-N⁵-acetyl-N⁵-benzyloxy-L-ornithinyl-glycine 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 以91%的产率得到allyl N²-(2,3-dibenzyloxybenzoyl)aminohexanoylcarbonyl-N⁵-acetyl-N⁵-benzyloxy-L-ornithinyl-glycinyl-L-3-(N-acetyl-N-benzyloxy)aminoalaninate
  参考文献：
  名称：

  Design and synthesis of a novel protected mixed ligand siderophore

  摘要：

  A novel siderophore analog (4) has been designed to facilitate iron transport-mediated drug delivery and drug release. This mixed ligand siderophore analog includes three bidentate ligands intended to octahedrally coordinate iron (III). The ligands include a 2,3-dihydroxy benzoic acid moiety, N(5)-acetyl-N(5)-hydroxy-L-ornithine, and a beta-N-hydroxy-alpha,beta-diaminopropionic acid derivative. The total synthesis of 15, a form of 4 that is suitably protected, yet contains a free carboxylic acid for subsequent drug conjugation, is described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.007